Celebrate Sweetest Day with Your Sweetie
Romantic ways to spend Saturday, October 19
Sweetest Day is a great excuse to show your love and appreciation to your partner. Whether you’re planning in advance or just remembered this Hallmark holiday, we’ve got your back. Make Saturday, October 19, a day to remember for you and your sweetie.
Let’s dive into the sweetest ideas for celebrating!
You might also like our date night guide.
Chicago Riverwalk Stroll & Heart-Shaped Pizza
Go for a late morning or early afternoon stroll around the River Walk and then stop by Pizzeria Portofino and surprise your special person with a heart-shaped pizza. On Sweetest Day, you can have any pizza shaped into a heart for $5, plus tax (gratuity not included).
Make a Sweetest Day reservation at Pizzeria Portofino.
Tea for Two
Get cozy at an Autumn Afternoon Tea at Mon Ami Gabi – Lincoln Park. On Saturday, October 19, from 1:00 PM – 3:00 PM, delight in the season with freshly brewed Rare Tea Cellar beverages, paired tea sandwiches, and pastries. Tickets are $70 per adult and $24.95 per child 12 and under, plus tax and 20% gratuity. Elevate your afternoon with Sparkling Brut, Sparkling Rosé, or the High Tea Spritz cocktail, available as add-ons for additional pricing.
Reserve tickets to Autumn Afternoon Tea at Mon Ami Gabi – Lincoln Park
Romance + Rum Flights
For your cocktail lover, head to The Bamboo Room at Three Dots and a Dash for a guided rum tasting. After taking your taste buds on a tropical tour around the world, get nostalgic over the award-winning cocktail bar’s inventive new menu, featuring whimsical creations like Ants on a Log and Root Beer Float.
Make a Sweetest Day reservation at The Bamboo Room.
Sweets for the Sweet
If your sweetheart is a pastry lover, take them on a coffee date to Beatrix! With locations near the Chicago River, some of the city’s best museums, and your fave shopping destinations (including in the ‘burbs at Beatrix at Oakbrook Center), grab seasonal specials like the Dulce de Leche Chai Cider and gluten-free Pumpkin Cream Cheese Coffeecake to-go and take a leisurely lovers’ stroll.
Make a Sweetest Day reservation at the Beatrix location nearest you.
Wine Tasting
Whisk your sweetest away to California’s Wine Country without leaving Chicago! The Cellar Door at the Oakville Grill & Cellar emulates the rustic feel of Napa Valley’s exquisite vineyards, and this October they are featuring pours from Round Pond Estate. For $65 per person, plus tax (gratuity not included), enjoy this wine-tasting experience. You can add a chef-curated cheese & salumi pairing available for an additional cost.
Make a Sweetest Day reservation for The Cellar Door tasting experience.
Curated Dinner for Two
For those looking for a unique tasting menu experience, opt for the RPM Sommelier Experience. Hosted by RPM Italian – Las Vegas and RPM Seafood, you’ll enjoy a guided tasting of expertly paired wine and food menus. The best part? No bottle is off-limits. You might be sipping vintage Champagne, Grand Cru Burgundies, and more. Plus, the executive chefs at both restaurants create menus that change daily to match the expertly chosen wines.
Book the Sommelier Experience for Sweetest Day at RPM Italian – Las Vegas.
Book the Sommelier Experience for Sweetest Day at RPM Seafood.
18-Course Omakase Experience
For the foodie in your life, consider The Omakase Room at Sushi-san. You’ll enjoy a one-of-a-kind 18-course menu from Master Chef Kaze Chan, starting at $250 per person (plus tax). Add the beverage pairing of your choice (sake, wine, non-alcoholic) and you’re in for a culinary journey.
Make a Sweetest Day reservation at The Omakase Room.
Start A New Tradition
As you may have heard, oysters are for lovers, and the couple that slurps together, stays together. So, start a new tradition with a sip and slurp at Shaw’s Oyster Bar! With a half-dozen varieties of East and West Coast oysters available daily, it’s a surefire to make every Sweetest Day shuckin’ delicious.
Make a reservation at Shaw’s – Chicago.
Make a reservation at Shaw’s – Schaumburg.
Brunch & Gift Shopping
Make your Sweetest Day in Orlando extra magical with brunch at Summer House on the Lake at Disney Springs! The gorgeous indoor-outdoor restaurant has menu of hearty coastal California-inspired brunch dishes like the Vegan Breakfast Burrito, Mexican Hash Browns, Pancake Tacos and more. On your way out, stop at The Cookie Bar for a sweet treat and a glass of Summer House Rosé to-go for a day of outdoor shopping!
Make a Sweetest Day reservation at Summer House on the Lake.
Treat your sweetie to a luxury shopping spree at Miami’s Bal Harbour Shops, but first—brunch! Head to Aba Miami – Bal Harbour for a Mediterranean brunch and refreshing cocktails including zero-proof options. (You might even spot a celebrity couple at the next table!)
Make a Sweetest Day reservation at Aba Miami – Bal Harbour.
In the Metro D.C. Area? Go to Wildfire – Tysons for brunch followed by shopping at Tysons Galleria.
Make a Sweetest Day reservation at Wildfire – Tysons.
Dessert with a View
Put a sweet finish on your Sweetest Day dinner at Miru with mouthwatering desserts like the Coconut-Mango Mousse, Calamansi Crème Brûlée and signature Black Sesame Mochi, made with charcoal-vanilla ice cream, black sesame praline, and mochi sponge cake. It’s dessert heaven, complete with stunning and romantic views of Chicago.
Make a Sweetest Day reservation at Miru.
Vegas Getaway
For a truly unforgettable and unexpected Sweetest Day, consider a surprise trip to the dazzling lights of Las Vegas. Whether you’re looking for world-class entertainment, gourmet dining at Eiffel Tower Restaurant, or a club night, Vegas has it all. Plan your escape and indulge in the excitement of Sin City with your sweetheart. View the Lettuce Vegas Vacation guide for more ideas.
Make a Sweetest Day reservation at Eiffel Tower Restaurant.
Cozy Night In
Sometimes, the most romantic moments happen at home. Plan a cozy night in with your loved one. Light some candles, order in or cook a special meal together (click here to explore our many recipes!), and enjoy a movie marathon. It’s all about creating a warm and intimate atmosphere.
(Does your partner like a good candle? Aba, Pizzeria Portofino and RPM Restaurants all offer signature scented candles for purchase.)
You can also order carryout or delivery from our restaurants, which is easier than ever through the LettuceEats® app.
Sweetest Day from Afar
But what if your sweetie is miles away? Sweetest Day can still be special. Send a surprise delivery, like a heartfelt letter and a basket with their favorite treats, to let them know you’re thinking of them. Here are some of our favorite treats available for Nationwide shipping. Plus you can include a Lettuce Gift Card so they can visit their favorite restaurant! Distance may separate you, but love knows no bounds.
